People would certainly think it was strange. Just not as strange. Besides, I think you know why its strange. Just like everything else…its strange because its not done. Why don’t people wear bras on the outside of shirts? It would work, but it would be strange.

Your comparison makes you sound ridiculous. It is done. This is a photograph of someone doing it. This is something particularly difficult for people, a man who looks like a man in womens clothes. I love the Sartorialist but remember it is a documentation of beautiful but generally very safe fashion. There are loads of people wearing much more outrageous gender questioning clothes than is shown on here. Wake up and look around you.

A beautiful person with beautiful clothes (i’m not totally sure if it is a man or women, no offence meant)

I love that nothing about this photograph fits our gender expectations or socialized perceptions. His feet are incredibly delicate, as are his hands, and his clothing choice is unique on its own, and then there is the very “masculine” ( in our N. American culture )of the shaved head. Beautiful capture. Quite thoughtful.

Comments like this are fascinating because they show just how un-evolved and pre-programmed our minds can be. If the product in this image looks beautiful as you rightly point out, then why is that beauty suddenly lost because a man is wearing it? Surely, your praise of the items is in some way (even if subconsciously) connected to how the person models them? This same ensemble wouldn’t look half as good on a 50 stone woman, trust me. Free your mind 33….

Yes I’ve been looking for a few days now and I still don’t know if I like it…But I keep coming back, compelled! It’s such an unexpected take on androgynous. It’s a low key kind of femininity mixed with low key masculinity… Not the usual amped up statement. It makes me think. Must be a good thing eh?

I don’t think it matters whether or not this is a man (woman express their sexuality by dressing how they please, why shouldn’t men be able to?) but has anyone considered that it might be a woman with a short haircut and masculine features? The person’s feet and hands are very delicate so lets not make assumptions… Either way, the androgyny makes this photo far more interesting than a simple photo of an outfit!

It’s rare to see a cross dressing man with good taste and a sense of style. I’m inclined to believe this particular gentleman is in fact motivated by style and a love of fashion rather than the desire to wear anything as long as its women’s clothing.

I keep popping back to this photo. To be honest, I donÂ´t know what to make of it! It almost looks like youÂ´ve manipulated his head on this body. The hands and feet donÂ´t seem to match his head- which is very masculine in bone structure. It doesnÂ´t seem to compute. But, I guess I choose to look it as art. ITÂ´S A FORM OF ART. Challenging….definitely…CHALLENGING -our perception of what seems….”correct!” Thanks Scott!

The only thing that worries me is that he looks worried. It would make so much difference if he looked as if he was enjoying his look. So many cross dressers do seem to look worried. Not surprisingly – it can be a precarious business.

I love his coat and sandals. Such a change from the usual uniform. But that’s a funny way to hold a bag.

Different strokes for different folks. BUT, while this may work in Milan, there are so, so many places in our world where it would not. And, the first thing that pops into my mind is that “realistically” the world is not ready for this and while this man is brave, would it be “wise” to walk around town like this where most of us live?

Thanks Scott so much for taking this amazing photo of me !!!!!!! And thanks everyone commenting here !!!!!!!! To me, fashion is what I enjoy wearing… I never ever care it’s for men or women..that will never be my thing.